Anti-herpesvirus agents: a patent and literature review (2003 to present)

Bibliography

• Chiu W, Rixon FJ. High resolution structural studies of complex icosahedral viruses: a brief overview. Virus Res 2002;82:9-17
   Google Scholar
• Gibson W. Structure and assembly of the virion. Intervirology 1996;39:389-400
   Google Scholar
• McGeoch DJ, Dolan A, Ralph AC. Toward a comprehensive phylogeny for mammalian and avian herpesviruses. J Virol 2000;74:10401-6
   PubMed Web of Science ®Google Scholar
• Arvin A, Campadelli-Fiume G, Mocarski E, et al. Human herpesviruses biology, therapy, and immunoprophylaxis. Cambridge University Press; Cambridge, UK: 2007
   Google Scholar
• Whitley RJ. Medical microbiology. University of Texas Medical Branch at Galveston; Galveston, TX, USA: 1996
   Google Scholar
• Ton L. Viral proteases. Chem Rev 2002;102:4609-26
   Google Scholar
• Holwerda BC. Herpesvirus proteases: targets for novel antiviral drugs. Anti Res 1997;35:1-21
   PubMedGoogle Scholar
• Gnann JW Jr, Barton NH, Whitley RJ. Aciclovir: mechanism of action, pharmacokinetics, safety and clinical applications. Pharmacotherapy 1983;3:275-83
   PubMed Web of Science ®Google Scholar
• Matthews T, Boehme R. Antiviral activity and mechanism of action of ganciclovir. Rev Infect Dis 1988;10:S490-4
   PubMedGoogle Scholar
• De Clercq E. Clinical potential of the acyclic nucleoside phosphonates cidofovir, adefovir, and tenofovir in treatment of DNA virus and retrovirus infections. Clin Microbiol Rev 2003;16:569-96
   PubMed Web of Science ®Google Scholar
• Earnshaw DL, Bacon TH, Darlison SJ, et al. Mode of antiviral action of penciclovir in MRC-5 cells infected with herpes simplex virus type 1 (HSV-1), HSV-2, and varicella-zoster virus. Antimicrob Agents Chemother 1992;36:2747-57
   PubMed Web of Science ®Google Scholar
• Crumpacker CS. Mechanism of action of foscarnet against viral polymerases. Am J Med 1992;92:3S-7
   PubMed Web of Science ®Google Scholar
• Susan JK, Therese M, Chapman D, et al. Brivudin (Bromovinyl Deoxyuridine). Drugs 2004;64:2091-7
   Google Scholar
• Kendle JB, Fan-Havard P. Cidofovir in the treatment of cytomegaloviral disease. Ann Pharmacother 1998;32:1181-92
   PubMed Web of Science ®Google Scholar
• Jabs DA, Enger C, Dunn J, et al. Cytomegalovirus retinitis and viral resistance: ganciclovir resistance. J Infect Dis 1998;177:770-3
   PubMed Web of Science ®Google Scholar
• Field AK. Human cytomegalovirus: challenges opportunities and new drug development. Antivir Chem Chemother 1999;10:219-32
   PubMed Web of Science ®Google Scholar
• Fader L, Lepage O, Bailey M, et al. Naphthyridinone derivatives as inhibitors of cytomegalovirus DNA polymerase. WO2013152063 A1; 2013
   Google Scholar
• Williams-Aziz SL, Hartline CB, Harden EA, et al. Comparative activities of lipid esters of cidofovir and cyclic cidofovir against replication of herpesviruses in vitro. Antimicrob Agents Chemother 2005;49:3724-33
   PubMed Web of Science ®Google Scholar
• Wan WB, Beadle JR, Hartline C, et al. Comparison of the antiviral activities of alkoxyalkyl and alkyl esters of cidofovir against human and murine cytomegalovirus replication in vitro. Antimicrob Agents Chemother 2005;49:656-62
   PubMed Web of Science ®Google Scholar
• Jiang ZG, Cohen J, Marshall LJ, Major EO. Hexadecyloxypropyl-cidofovir (CMX001) suppresses JC virus replication in human fetal brain SVG cell cultures. Antimicrob Agents Chemother 2010;54:4723-32
   PubMed Web of Science ®Google Scholar
• Hostetler KY, Beadle JR, Kini GD. Phosphonate compounds. CA2747954 A1; 2001
   Google Scholar
• De Clercq E, Field HJ. Antiviral prodrugs—the development of successful prodrug strategies for antiviral chemotherapy. Br J Pharmacol 2006;147:1-11
   PubMed Web of Science ®Google Scholar
• Ng TI, Shi Y, Huffaker HJ, et al. Selection and characterization of varicella-zoster virus variants resistant to (R)-9-[4-hydroxy-2-(hydroxymethy)butyl]guanine. Antimicrob Agents Chemother 2001;45:1629-36
   PubMed Web of Science ®Google Scholar
• Akesson-Johansson A, Harmenberg J, Wahen B, Linde A. In-hibition of human herpesvirus 6 replication by 9-[4-hydroxy-2-(hydroxymethyl)butyl]guanine (2HM-HBG) and other antiviral compounds. Antimicrob Agents Chemother 1990;34:2417-19
   PubMedGoogle Scholar
• Abele G, Karlstrom A, Harmenberg J, et al. Inhibiting effect of (R,S)-9-[4-hydroxy-(hydroxymethyl)butyl]guanine on varicella–zoster virus replica-tion in cell culture. Antimicrob Agents Chemother 1987;31:76-80
   PubMed Web of Science ®Google Scholar
• Andrei G, Snoeck R, Reymen D, et al. Comparative activity of selected antiviral compounds against clinical isolates of varicella-zoster virus. Eur J Clin Microbiol Infect Dis 1995;14:318-29
   PubMed Web of Science ®Google Scholar
• Lowe DM, Alderton WK, Ellis MR, et al. Mode of action of [(R)-9-{4-hydroxy-2- (hydroxymethyl)butyl}-guanine] against herpesviruses. Antimicrob Agents Chemother 1995;39:1802-8
   PubMed Web of Science ®Google Scholar
• Kern ER, Bidanset DJ, Hartline CB, et al. Oral activity of a methylenecyclopropane analog, cyclopropavir, in animal models for cytomegalovirus infections. Antimicrob Agents Chemother 2004;48:4745-53
   PubMed Web of Science ®Google Scholar
• Nassiri MS, Emerson R, Devivar L, et al. Comparison of benzimidazole nucleosides and ganciclovir on the in vitro proliferation and colony formation of human bone marrow progenitor cells. Br J Haematol 1996;93:273-9
   PubMedGoogle Scholar
• Townsend LR, Devivar S, Turk M, et al. Design, synthesis, and antiviral activity of certain 2,5,6-trihalo-1-(D-ribofuranosyl)benzimidazoles. J Med Chem 1995;38:4098-105
   PubMed Web of Science ®Google Scholar
• Chamberlain SD, Daluge SM, Koszalka GW. Antiviral benzimidazole nucleoside analogues and a method for their preparation. US6077832A; 2000
   Google Scholar
• Biron KK, Harvey RJ, Chamberlain SC, et al. Potent and selective inhibition of human cytomegalovirus replication by 1263W94, a benzimidazole-L-riboside with a unique mode of action. Antimicrob Agents Chemother 2002;46:2365-72
   PubMed Web of Science ®Google Scholar
• Krosky PM, Baek MC, Coen DM. Human cytomegalovirus UL97 protein kinase, an antiviral drug target, is required at the stage of nuclear egress. J Virol 2003;77:905-14
   PubMed Web of Science ®Google Scholar
• Wolf DG, Courcelle CT, Prichard MN, et al. Distinct and separate roles for herpesvirus-conserved UL97 kinase in cytomegalovirus DNA synthesis and encapsidation. Proc Natl Acad Sci USA 2001;98:1895-900
   PubMedGoogle Scholar
• Chacko B, John GT. Leflunomide for cytomegalovirus: bench to bedside. Transpl Infect Dis 2012;14:111-20
   PubMed Web of Science ®Google Scholar
• Tong L, Qian C, Massariol MJ, et al. A new serine-protease fold revealed by the crystal structure of human cytomegalovirus protease. Nature 1996;383:272-5
   PubMedGoogle Scholar
• Qiu X, Culp JS, DiLella AG, et al. Unique fold and active site in cytomegalovirus protease. Nature 1996;383:275-9
   Google Scholar
• Shieh HS, Kurumbail RG, Stevens AM, et al. Three-dimensional structure of human cytomegalovirus protease. Nature 1996;383:279-82
   PubMed Web of Science ®Google Scholar
• Chen P, Tsuge H, Almassy RJ, et al. Structure of the human cytomegalovirus protease catalytic domain reveals a novel serine protease fold and catalytic triad. Cell 1996;86:835-43
   PubMedGoogle Scholar
• Qiu X, Janson CA, Culp JS. Crystal structure of varicella-zoster virus protease. Proc Natl Acad Sci USA 1997;94:2874-9
   PubMedGoogle Scholar
• Hoog SS, Smith WW, Qiu X. Active site cavity of herpesvirus proteases revealed by the crystal structure of herpes simplex virus protease/inhibitor complex. Biochemistry 1997;36:14023-9
   Google Scholar
• Reiling KK, Pray TR, Craik CS. Functional consequences of the Kaposi’s sarcoma-associated herpesvirus protease structure: regulation of activity and dimerization by conserved structural elements. Biochemistry 2000;39:12796-803
   Google Scholar
• Lee GM, Shahian T, Baharuddin A, et al. Enzyme inhibition by allosteric capture of an inactive conformation. J Mol Biol 2011;411:999-1016
   Google Scholar
• Liu FY, Roizman B. The herpes simplex virus 1 gene encoding a protease also contains within its coding domain the gene encoding the more abundant substrate. J Virol 1991;65:5149-56
   PubMedGoogle Scholar
• Welch AR, Woods AS, McNally LM, et al. A herpesvirus maturational proteinase, assemblin: identification of its gene, putative active site domain, and cleavage site. Proc Natl Acad Sci USA 1991;88:10792-6
   PubMedGoogle Scholar
• Preston VG, Coates JAV, Rixon FJ. Identification and characterization of a herpes simplex virus gene product required for encapsidation of virus DNA. J Virol 1983;45:1056-64
   PubMedGoogle Scholar
• Corey DR, Craik CS. An investigation into the minimum requirements for peptide hydrolysis by mutation of the catalytic triad of trypsin. J Am Chem Soc 1992;114:1784-90
   Google Scholar
• Khayat R, Batra R, Bebernitz GA, et al. Characterization of the monomer-dimer equilibrium of human cytomegalovirus protease by kinetic methods. Biochemistry 2004;43:316-22
   Google Scholar
• Carter P, Wells JA. Dissecting the catalytic triad of a serine protease. Nature 1988;332:564-8
   PubMedGoogle Scholar
• Khayat R, Batra R, Massariol MJ. Investigating the role of histidine 157 in the catalytic activity of human cytomegalovirus protease. Biochemistry 2001;40:6344-51
   Google Scholar
• Schmidt U, Darke PL. Dimerization and activation of the herpes simplex virus type 1 protease. J Biol Chem 1997;272:7732-5
   PubMed Web of Science ®Google Scholar
• Yamanaka G, DiIanni CL, O’Boyle DR, et al. Stimulation of the herpes simplex virus type I protease by antichaeotrophic salts. J Biol Chem 1995;270:30168-72
   Google Scholar
• Batra R, Khayat R, Tong L. Molecular mechanism for dimerization to regulate the catalytic activity of human cytomegalovirus protease. Nat Struct Biol 2001;8:810-17
   PubMedGoogle Scholar
• Tong L, Qian C, Massariol MJ. Conserved mode of peptidomimetic inhibition and substrate recognition of human cytomegalovirus protease. Nat Struct Biol 1998;5:819-26
   PubMedGoogle Scholar
• LaPlante SR, Aubry N, Bonneau PR. Human cytomegalovirus protease complexes its substrate recognition sequences in an extended peptide conformation. Biochemistry 1998;37:9793-801
   Google Scholar
• Gibson W, Welch AR, Hall MT. Assembling a herpes virus serine maturational proteinase and new molecular target for antivirals. Perspect Drug Discov 1995;2:413-26
   Google Scholar
• Ogilvie W, Bailey M, Poupart MA, et al. Peptidomimetic inhibitors of the human cytomegalovirus protease. J Med Chem 1997;40:4113-35
   Google Scholar
• Batra R, Khayat R, Tong L. Structural studies of herpesvirus proteases. Protein Peptide Lett 2001;8:333-42
   Google Scholar
• LaPlante SR, Bonneau PR, Aubry N, et al. Characterization of the human cytomegalovirus protease as an induced-fit protease and the implications to the design of mechanism-based peptidyl inhibitors. J Am Chem Soc 1999;21:2974-86
   Google Scholar
• Marnett AB, Nomura AM, Shimba N, et al. Communication between the active sites and dimer interface of a herpesvirus protease revealed by a transition-state inhibitor. Proc Natl Acad Sci USA 2004;101:6870-5
   Google Scholar
• Nomura AM, Marnett AB, Shimba N, et al. One functional switch mediates reversible and irreversible inactivation of a herpesvirus protease. Biochemistry 2006;45:3572-9
   Google Scholar
• Lazic A, Goetz DH, Nomura AM, et al. Substrate modulation of enzyme activity in the herpesvirus protease family. J Mol Biol 2007;373:913-23
   Google Scholar
• Shahian T, Gregory ML, Lazic A. Inhibition of a viral enzyme by a small molecule dimer disruptor. Nat Chem Biol 2009;5:640-6
   PubMed Web of Science ®Google Scholar
• Gantt S, Carlsson J, Ikoma M, et al. The HIV protease inhibitor nelfinavir inhibits Kaposi’s sarcoma-associated herpesvirus replication in vitro. Antimicrob Agents Chemother 2011;55:2696-703
   Google Scholar
• Kalu NN, Desai PJ, Shirley CM, et al. Nelfinavir inhibits maturation and export of herpes simplex virus 1. J Virol 2014;88:5455-61
   Google Scholar
• Gantt S, Cattamanchi A, Krantz E, et al. Reduced human herpesvirus-8 oropharyngeal shedding associated with protease inhibitor-based antiretroviral therapy. J Clin Virol 2014;60:127-32
   Google Scholar
• Borthwick AD. Design of translactam HCMV protease inhibitors as potent antivirals. Med Res Rev 2005;25:427-52
   PubMed Web of Science ®Google Scholar
• Borthwick AD, Angier SJ, Crame AJ, et al. Design and synthesis of pyrrolidine-5,5-trans-lactams (5-oxo-hexahydro-pyrrolo[3,2-b]pyrroles) as novel mechanism-based inhibitors of human cytomegalovirus protease. 1. The alpha-methyl-trans-lactam template. J Med Chem 2000;43:4452-64
   PubMedGoogle Scholar
• Gerona-Navarro G, Perez de Vega MJ, Garcia-Lopez MT, et al. Synthesis and anti-HCMV activity of 1-acyl-beta-lactams and 1-acylazetidines derived from phenylalanine. Bioorg Med Chem Lett 2004;14:2253-6
   PubMed Web of Science ®Google Scholar
• Gerona-Navarro G, Perez de Vega MJ, Garcia-Lopez MT, et al. From 1-acyl-beta-lactam human cytomegalovirus protease inhibitors to 1-benzyloxycarbonylazetidines with improved antiviral activity. A straightforward approach to convert covalent to noncovalent inhibitors. J Med Chem 2005;48:2612-21
   PubMed Web of Science ®Google Scholar
• Perez-Faginas P, Aranda MT, Garcia-Lopez MT, et al. Synthesis and SAR studies on azetidine-containing dipeptides as HCMV inhibitors. Bioorg Med Chem 2011;19:1155-61
   Google Scholar
• Di Grandi MJ, Curran KJ, Baum EZ, et al. Pyrimido[1,2-b]-1,2,4,5-tetrazin-6-ones as HCMV protease inhibitors: a new class of heterocycles with flavin-like redox properties. Bioorg Med Chem Lett 2003;13:3483-6
   PubMedGoogle Scholar
• Flynn DL, Zablocki J, Williams K, et al. Electrophilic ketones for the treatment of herpesvirus infections. US6673784 B1; 2004
   Google Scholar
• Sabit H, Dahan A, Sun J. Cytomegalovirus protease targeted prodrug development. Mol Pharm 2013;10:1417-24
   Google Scholar
• Boehmer PE, Lehman IR. Herpes simplex virus DNA replication. Annu Rev Biochem 1997;66:347-84
   PubMed Web of Science ®Google Scholar
• Crute JJ, Tsurumi T, Zhu LA, et al. Herpes simplex virus 1 helicase-primase: a complex of three herpes-encoded gene products. Proc Natl Acad Sci USA 1989;86:2186-9
   Google Scholar
• Spector FC, Liang L, Giordano H, et al. Inhibition of herpes simplex virus replication by a 2-amino thiazole via interactions with the helicase component of the UL5-UL8-UL52 complex. J Virol 1998;72:6979-87
   PubMed Web of Science ®Google Scholar
• Kleymann G, Fischer R, Betz UA, et al. New helicase-primase inhibitors as drug candidates for the treatment of herpes simplex disease. Nat Med 2002;8:392-8
   PubMed Web of Science ®Google Scholar
• Wald A, Corey L, Timmler B, et al. Helicase-primase inhibitor pritelivir for HSV-2 infection. N Engl J Med 2014;370:201-10
   PubMed Web of Science ®Google Scholar
• Biswas S, Field HJ. Herpes simplex virus helicase-primase inhibitors: recent findings from the study of drug resistance mutations. Antivir Chem Chemother 2008;19:1-6
   PubMedGoogle Scholar
• Birkmann A, McCormick D, Kropelt D, et al. Excellent efficacy and pharmacokinetics have been demonstrated in preclinical and phase I/II studies by AIC316, a novel drug against herpes simplex (HSV) type 1 and 2 (abstract 48). Abstracts of the 25th International Conference on Antiviral Research; 16 – 29 April 2012; Sapporo, Japan
   Google Scholar
• Crute JJ, Grygon CA, Hargrave KD, et al. Herpes simplex virus helicase-primase inhibitors are active in animal models of human disease. Nat Med 2002;8:386-91
   PubMed Web of Science ®Google Scholar
• Tyring S, Wald A, Zadeikis N, et al. ASP2151 for the treatment of genital herpes: a randomized, double-blind, placebo- and valaciclovir-controlled, dose-finding study. J Infect Dis 2012;205:1100-10
   PubMed Web of Science ®Google Scholar
• Chono K, Katsumata K, Kontani T, et al. ASP2151, a novel helicase-primase inhibitor, possesses antiviral activity against varicellazoster virus and herpes simplex virus types 1 and 2. J Antimicrob Chemother 2010;65:1733-41
   PubMed Web of Science ®Google Scholar
• Lischka P, Hewlett G, Wunberg T, et al. In vitro and in vivo activities of the novel anticytomegalovirus compound AIC246. Antimicrob Agents Chemother 2010;54:1290-7
   PubMed Web of Science ®Google Scholar
• Bogner E. Human cytomegalovirus terminase as a target for antiviral chemotherapy. Rev Med Virol 2002;12:115-27
   PubMed Web of Science ®Google Scholar
• Goldner T, Hewlett G, Ettischer N, et al. The novel anticytomegalovirus compound AIC246 (Letermovir) inhibits human cytomegalovirus replication through a specific antiviral mechanism that involves the viral terminase. J Virol 2011;85:10884-93
   PubMed Web of Science ®Google Scholar
• Kaul DR, Stoelben S, Cober E, et al. Report of successful treatment of multidrug-resistant cytomegalovirus disease with the novel anti-CMV compound AIC246. Am J Transpl 2011;11:1079-84
   PubMed Web of Science ®Google Scholar
• Nadal M, Mas PJ, Blanco AG, et al. Structure and inhibition of herpesvirus DNA packaging terminase nuclease domain. Proc Natl Acad Sci USA 2010;14:16078-83
   Google Scholar
• Schubart D, Habenberger P, Stein-Gerlach M, Bevec D. Cellular kinases involved in Cytomegalovirus infection and their inhibition. US6849409 B2; 2001
   Google Scholar
• Proesch S, Volk HD, Krueger D. Proteaseome inhibitors for the treatment of herpesviridae infected individuals. WO2004004749 A1; 2004
   Google Scholar
• Rivetta AJ, Gardner RC. Proteasome inhibitors: from in vitro uses to clinical trials. J Pept 2000;6:478-88
   Google Scholar
• Schwarz K, de Giuli R, Schmidtke G, et al. The selective proteasome inhibitors lactacystin and epoxomicin can be used to either up- or down-regulate antigen presentation at nontoxic doses. J Immunol 2000;164:6147-57
   PubMed Web of Science ®Google Scholar
• Wiertz EJ, Jones TR, Sun L, et al. The human cytomegalovirus US11 gene product dislocates MHC class I heavy chains from the endoplasmic reticulum to the cytosol. Cell 1996;84:769-79
   PubMed Web of Science ®Google Scholar
• Balzarini J, Camarasa MJ, Velazquez S. Compositions for the treatment or prophylaxis of viral infections. US8513215 B2; 2013
   Google Scholar
• Balzarini J. Prodrugs cleavable by cd26. WO2004098644 A1; 2004
   Google Scholar
• De Castro S, García-Aparicio C, Andrei G, et al. 4-Benzyloxy-gamma-sultone derivatives: discovery of a novel family of non-nucleoside inhibitors of human cytomegalovirus and varicella zoster virus. J Med Chem 2009;52:1582-91
   PubMed Web of Science ®Google Scholar
• Wunberg T, Baumeister J, Jesko M, et al. Substituted quinazolines as antiviral agents, especially against cytomegalovirus. US2006/0235032 A1; 2006
   Google Scholar
• Kontani T, Miyata J, Hamaguchi W, et al. Tetrahydro-2H-thiopyran-4-carboxamide derivative. US6903125 B2; 2005
   Google Scholar
• Kenneth BF, Lowden CT. Acridone derivatives as anti-herpesvirus agents. WO2005023178 A2; 2005
   Google Scholar
• He R, Mott BT, Rosenthal AS, et al. Anartemisinin-derived dimer has highly potent anti-cytomegalovirus (CMV) and anti-cancer activities. PLoS One 2011;6:e24334
   PubMed Web of Science ®Google Scholar
• Pagliara D, Savoldo B. Cytotoxic T lymphocytes for the treatment of viral infections and posttransplant lymphoproliferative disorders in transplant recipients. Curr Opin Infect Dis 2012;25:431-7
   Google Scholar